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- W2951773392 abstract "Solvolysis of (E)- and (Z)-2-methyl-5-phenyl-1-pentenyl(phenyl)iodonium tetrafluoroborate (1·BF4) was carried out in various alcohols, acetic acid, and aqueous solutions at 60 °C. Products (after acid hydrolysis) include iodobenzene and 2-methyl-5-phenylpentanal as well as rearranged ones: 6-phenyl-2-hexanone, 6-phenyl-3-hexanone, 6-phenyl-2-hexyne, 6-phenyl-1,2-hexadiene, and 6-phenyl-2,3-hexadiene. The products of α-elimination, including 1-methyl-3-phenyl-1-cyclopentene, were also obtained in methanol and ethanol. Solvolysis of the E isomer (E)-1 is faster than that of (Z)-1 in every solvent examined. The percentage of rearrangement is higher with (E)-1 than with (Z)-1, and the main rearranged products are those of migration of the alkyl group trans to the iodonio group, but migration of the cis alkyl group is also involved. Theoretical calculations suggest that interconversion between the secondary vinylic cations by 1,2-hydride shift is rapid. These results show that a major heterolysis reaction occu..." @default.
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- W2951773392 date "1999-12-01" @default.
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- W2951773392 title "Solvolysis of 2,2-Dialkylvinyl Iodonium Salt: Alkyl Participation and Possibility of a Primary Vinylic Cation Intermediate" @default.
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